Isopropyl iodide → HCID 22497250, compound

Temperature

25 °C

A solution of 2,2,2-trifluoro-1-(6-trifluoromethyl-1H-indol-3-yl)-ethanone (1.0 g, 3.56 mmol) in N,N-dimethylformamide (10 mL) at 25° C. was treated with potassium carbonate (1.22 g, 8.89 mmol). The resulting mixture was stirred at 25° C. for 10 min. At this time, the reaction was treated with 2-iodopropane (0.53 mL, 5.34 mmol). The reaction was heated at 65° C. for 4 h. At this time, the reaction was cooled to 25° C. and was partitioned between water (75 mL) and ethyl acetate (75 mL). The organic layer was washed with a 1N aqueous hydrochloric acid solution (1×25 mL), water (1×50 mL), and a saturated aqueous sodium chloride solution (1×50 mL). The organic layer was then dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 2,2,2-trifluoro-1-(1-isopropyl-6-trifluoromethyl-1H-indol-3-yl)-ethanone (850 mg, 74%) as a pale orange solid: mp 92-93° C.; EI-HRMS m/e calcd for C14H11F6NO (M+) 323.0745, found 323.0739.

1. temperatureThe reaction was heated at 65° C. for 4 h
2. temperatureAt this time, the reaction was cooled to 25° C.
3. customwas partitioned between water (75 mL) and ethyl acetate (75 mL)
4. washThe organic layer was washed with a 1N aqueous hydrochloric acid solution (1×25 mL), water (1×50 mL)
5. dry with materialThe organic layer was then dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-75cc6be65a744f46ad68b5968b78e954

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06881844B2